题名

分別以氫氧化鈉及脂解酶催化甘油解法製備富含雙甘油酯大豆油之最適條件之探討

并列篇名

Study on The Optimum Conditions for Preparing of Diacylglycerol–Enriched Soybean by Sodium Hydroxide and Lipase Catalyzed Glycerolysis

DOI

10.6578/TJACFS.201904_57(2).0001

作者

蔡羽豐(Yu-Feng Tsai);徐錫樑(Shyi-Liang Shyu)

关键词

雙甘油酯 ; 大豆油 ; 氫氧化鈉催化甘油解法 ; 脂解酶催化甘油解法 ; 管柱純化 ; Diacylglycerol ; Soybean oil ; Sodium hydroxide catalyzed glycerolysis ; Lipase catalyzed glycerolysis ; Column purification

期刊名称

臺灣農業化學與食品科學

卷期/出版年月

57卷2期(2019 / 04 / 01)

页次

61 - 71

内容语文

繁體中文

中文摘要

本研究主要探討大豆油以氫氧化鈉催化甘油解法(SHCG)與脂解酶催化甘油解法(LCG)製備雙甘油酯(diacylglycerol, DAG)。將製備之粗DAG以管柱區分進行純化,得到富含1,3-DAG。結果顯示,SHCG最適條件是將大豆油加入0.5莫耳比(甘油/油)之甘油於50℃下在氫氧化鈉催化反應2小時,並以丙酮作為溶劑。DAG的產量可達50.27%。上述條件,若以乙醇取代丙酮,其DAG的產量可達32.28%。LCG最適條件是將大豆油加入10%之脂肪酶,並加入0.5莫耳比(甘油/油)之甘油,於50℃下反應8小時,DAG的產量可達44.55%。粗DAG經由管柱純化之後,SHCG製備之1,3-DAG含量為43.09%,此結果表示約有90%的DAG是1,3-DAG。LCG製備之1,3-DAG含量則為31.18%,此結果表示約有70%之DAG為1,3-DAG。

英文摘要

This study was to investigate the diacylglycerol (DAG) prepared from soybean oil with sodium hydroxide catalyzed glycerolysis (SHCG) and lipase catalyzed glycerolysis (LCG). The crude DAG was purified by the column fractionation to obtain 1,3-DAG-enriched. The results showed that the optimal condition of SHCG was: glycerol/oil ratio of 0.5 mol, reaction temperature of 50°C, sodium hydroxide catalyzed reaction time of 2 hrs and acetone as solvent. The yield of DAG could reach up to 50.27% by using this reaction condition. The yield of DAG could reach 32.28% when acetone was substituted by ethanol under this condition. In addition, the optimal condition of LCG was: glycerol/oil ratio of 0.5 mol, reaction temperature of 50°C and reaction time of 8 hrs. The yield of DAG was maximized to 44.55% when DAG was prepared by this condition. After column purification, the 1,3-DAG content of the crude DAG prepared by SHCG was 43.09%. This result indicated that the content of 1,3-DAG was about 90% in purified DAG. On the other hand, the 1,3-DAG content of the crude DAG prepared by LCG was 31.18%. This result indicated that the content of 1,3-DAG was around 70% in purified DAG.

主题分类 生物農學 > 農業
生物農學 > 森林
生物農學 > 畜牧
生物農學 > 漁業
生物農學 > 農產加工
工程學 > 化學工業
参考文献
  1. Bellot, J. C.,Choisnard, L.,Castillo, E.,Marty, A.(2001).Combining solvent engineering and thermodynamic modeling to enhance selectivity during monoglyceride synthesis by lipase-catalyzed esterification.Enzyme and Microbial Technology,28,362-369.
  2. Berger, M.,Laumen, K.,Schneider, M. P.(1992).Enzymatic esterification of glycerol I lipase-catalyzed synthesis of regioisomerically pure 1,3-sn-diacylglycerols.Journal of the American Oil Chemists Society,69,955-960.
  3. Cai, C.,Gao, Y.,Liu, Y.,Zhong, N.,Liu, N.(2016).Immobilization of Candida antarctica lipase B onto SBA-15 and their application in glycerolysis for diacylglycerols synthesis.Food Chemistry,212,205-212.
  4. Cheong, L. Z.,Tan, C. P.,Long, K.,Yusoff, M. S. A.,Arifin, N.,Lo, S. K.,Lai, O. M.(2007).Production of a diacylglycerol-enriched palm olein using lipase-catalyzed partial hydrolysis: Optimization using response surface methodology.Food Chemistry,105,1614-1622.
  5. Dalonzo, R. P.,Kozarek, W. J.,Wade, R. L.(1982).Glyceride composition of processed fats and oils as determined by glass capillary gas chromatography.Journal of the American Oil Chemists Society Soc.,59,292-295.
  6. Damstrup, M. L.,Jensen, T.,Sparsø, F. V.,Kiil, S. Z.,Jensen, A. D.,Xu, X.(2006).Production of Heat-Sensitive Monoacylglycerols by Enzymatic Glycerolysis in tert-Pentanol: Process Optimization by Response Surface Methodology.Journal of the American Oil Chemists' Society,83,27-33.
  7. Damstrup, M. L.,Jensen, T.,Sparsø, F. V.,Kiil, S. Z.,Jensen, A. D.,Xu, X.(2005).Solvent optimization for efficient enzymatic monoacylglycerol production based on a glycerolysis reaction.Journal of the American Oil Chemists' Society,82,559-564.
  8. Duan, Z. Q.,Du, W.,Liu, D. H.(2010).Novozym 435-catalyzed 1,3-diacylglycerol preparation via esterification in t-butanol system.Process Biochem,45,1923-1927.
  9. Flickinger, B. D.,Matsuo, N.(2003).Nutritional characteristics of DAG oil.Lipids,38,129-132.
  10. Gruenwedel, D.(ed.),Whitaker, J. R.(ed.)(1985).Food Analysis Principles and Techniques.New York:Marcel Dekker.
  11. Guo, Z.,Sun, Y.(2007).Solvent-free production of 1,3-diglyceride of CLA:Strategy consideration and protocol design.Food Chemistry,100,1076-1084.
  12. Isabel, J.,Karina, V.,Alejandro, C.,Antonio, P.(2015).J. Isabel, V. Karina, C. Alejandro and P. Antonio: Process for obtaining vegetable oil rich in 1,3-diacylglycerols. European Patent, WO2016079671 A1 (2015)..
  13. Katsuragi, Y.(ed.),Yasukawa, T.(ed.),Matsuo, N.(ed.),Flickinger, I.(ed.),Tokimitsu(ed.),Matlock, M. G.(ed.)(2008).Diacylglycerol oil.Champaign, USA:AOCS Press.
  14. Kondo, H.,Hase, T.,Murase, T.,Ichiro, T.(2003).Digestion and assimilation features of dietary DAG in the rat small intestine.Lipids,38,25-30.
  15. Kristensen, J. B.,Xu, X.,Mu, H.(2005).Diacylglycerol synthesis by enzymatic glycerolysis: Screening of commercially available lipases.Journal of the American Oil Chemists' Society,82,329-334.
  16. Murata, M.,Hara, K.(1994).Alteration by diglycerols of the transport and fatty acid composition of lymph chylomcrons in rats.BioScience Biotech Biochemistry,58,1416-1419.
  17. Noureddini, H.,Harkey, D. W.,Gutsman, M. R.(2004).A continuous process for the glycerolysis of soybean oil.Journal of the American Oil Chemists Society,81,203-207.
  18. Pawongrat, R.,Xu, X.,H-Kittikun, A.(2007).Synthesis of monoacylglycerol rich in polyunsaturated fatty acidsfrom tuna oil with immobilized lipase AK.Food Chemistry,104,251-258.
  19. Pazdur, Ł.,Geuens, J.,Sels, H.,Tavernier, S. M. F.(2015).Low Temperature Chemical Synthesis of High Purity Diacylglycerols (DAG) from Monoacylglycerols (MAG).Lipids,50,219-226.
  20. Rosu, R.,Yasui, M.,Iwasaki, Y.,Yammane, T.(1999).Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system.Journal of the American Oil Chemists' Society,76,839-843.
  21. Shimizu, M.,Kohori, J.,Kase, M.,Watanabe, T.,Onozuka, K.(2003).M. Shimizu, J. Kohori, M. Kase, T. Watanabe and K. Onozuka: Process for the production of diglycerides. PCT Int. Appl. WO060139 (2003)..
  22. Stavarache, C.,Vinatoru, M.,Maeda, Y.(2006).Ultrasonic versus silent methylation of vegetable oils.Ultrasonics Sonochemistry,13,401-407.
  23. Stavarache, C.,Vinatoru, M.,Maeda, Y.(2007).Aspects of ultrasonically assisted transesterification of various vegetable oils with methanol.Ultrasonics Sonochemistry,14,380-386.
  24. Stavarache, C.,Vinatoru, M.,Nishimura, R.,Maeda, Y.(2005).Fatty acids methyl esters from vegetable oil by means of ultrasonic energy.Ultrasonics Sonochemistry,12,367-372.
  25. Tokimitsu, I.,Katsuragi, Y.,Yasukawa, T.,Matsuo, N.,Brent, D.,Mark, G.(2004).Diacylglycerol Oil.Journal of the American Oil Chemists' Society,3,30-45.
  26. Watanabe, T.,Shimizu, M.,Sugiura, M.,Sato, M.,Kohori, J.,Yamada, N.,Nakanishi, K.(2003).Optimization of reaction conditions for the production of DAG using immobilized 1,3-regiospecific lipase lipozyme RM IM.Journal of the American Oil Chemists' Society,80,1201-1207.
  27. Weber, N.,Mukherjee, K. D.(2004).Solvent-free Lipase-Catalyzed Preparation of Diacylglycerols.J. Agric. Food Chem.,52,5347-5353.
  28. Xu, X.,Mu, H.,Skands, A. R. H.,Høy, C. E.,Adler-Nissen, J.(1999).Parameters affecting diacylglycerol formation during the production of specific-structured lipids by lipase-catalyzed interesterification.Journal of the American Oil Chemists' Society,76,175-181.
  29. Yamada, Y.,Shimizu, M.,Sugiura, M.,Yamada, N.(1999).Y. Yamada, M. Shimizu, M. Sugiura and N. Yamada: Process for producing diglycerides. KAO CORP (JP) Ed. Patent WO9909119 (1999)..
  30. Yamane, T.,Kang, S. T.,Kawahara, K.,Koizumi, Y.(1994).High-yield diacylglycerol formation by solid-phase enzymatic glycerolysis of hydrogenated beef tallow.Journal of the American Oil Chemists’ Society,71,339-342.
  31. Yang, T.,Zhang, H.,Mu, H.,Sinclair, A. J.,Xu, X.(2004).Diacylglycerols from butterfat: Production by glycerolysis and short-path distillation and analysis of physical properties.Journal of the American Oil Chemists’ Society,81,979-987.
  32. Yasushi, Y.,Masami, S.,Masakatsu, S.,Naoto, Y.(1999).Y. Yasushi, S. Masami, S. Masakatsu and Y. Naoto: Process for producing diglycerides. PCT Int. Appl. WO9909119 (1999)..
  33. Zhong, N.,Li, L.,Xu, X.,Cheong, L. Z.,Xu, Z.,Li, B.(2013).High yield of monoacylglycerols production throughlow-temperature chemical and enzymatic glycerolysis.Eur. J. Lipid Sci. Technol.,115,684-690.
  34. 王誌宏(2000)。國立臺灣大學農業化學研究所。